Sam and Dean meet Blair Waldorf
by ColtLady
Summary: Supernatural/Gossip Girl crossover. A little out there I know but it just stuck in my head. Blair wants to escape and meets two handsome brothers while hitchhiking down the road.
1. On The Road

"Holy crap Sammy. What is that?" Dean asked jamming the breaks on the Impala as he spotted a gorgeous brunette on the side of the road with her thumb to the side.

"That's a girl Dean. I understand you don't recognize them with clothes on." Sam replied annoyed that he had been woken up for this. They had just finished a job and he was tired.

"I know Sam but damn they don't make em like that everywhere." Dean said admiring the girl's tiny waist and haughty attitude. "Let's take her for a ride. I call dibs." He announced pulling over and rolling down his window.

"Cute car, an antique." The girl said walking over. Dean barely noticed the insult to his car as he watched her hips move in her tight pencil skirt.

"Sammy, you know what a skirt like that says? Please fu..." That was as far as Dean got before Sam clapped a hand over his mouth and leaned forward towards the girl at the window.

"Sorry for my brother he was raised by gorillas. Did you need a ride somewhere." Sam asked.

"I told you the skirt already told me she needed a ride." Dean whispered. He was startled by the smack at his left side.

"Ouch!" He said glaring at the little tartlet at his side.

"This is an Eleanor Waldorf original it does not ask for sexual favors. Especially not from someone wearing, ugh, vintage or off the rack." The girl said making a face at Dean's coat. Sam started laughing he was liking this girl already.

"Well Miss Priss what can me and my ugly coat do for you?" Dean asked annoyed.

"I need to escape." She said. "I don't care to where. I have money. And a taser." The last comment she aimed at Dean. "You boys look like fun and fun is what I need." She said smiling. Sam looked at Dean who had already made up his mind how to bring the little tart down a few pegs.

"Hop in. Sammy'll sit in the back. Get the lady's bags Sam she is wearing a Ellie Wardoff original. We know just where to find the fun. But first pie and a cheeseburger, your treat." Dean said, Sam rolled his eyes and went to get the girl's bags.

"I'm Sam." He said "The pig is Dean."

"Blair Waldorf." She said swinging her brown curls at him and settling into the passenger seat.

_Two hours and many miles later_

"I can't believe they didn't have low-fat balsamic vinaigrette." Blair whined as she picked at her house salad. "I mean it's not even that great."

"This is small town USA not the Waldorf Astoria." Dean said his mouth full of cherry pie. "Are you sure you don't want some pie?" He asked.

"Ugh, no." Blair said wrinkling her nose.

"Suit yourself baby." Dean resumed stuffing his face full of pie. "So, Sammy what's the case?" He asked.

Sam glanced at Blair before beginning. "Are you sure you're up for this. It can get a little dirty." He said concerned.

"And he doesn't mean a wrinkle in your couture dirty." Dean said. "He means actual mud and dirt."

Blair glared at him. "I was looking for fun and something different. I can handle it." She said. They had already explained to her what they did. She didn't believe a word they said but she was willing to tag along because she was bored of the city and needed to get away from everything. How better then chasing ghosts, demons, and other things that didn't exist.

Sam shrugged and continued. "Phoenix, Arizona three people have turned up dead in the last month."

"Oh no, was it the boogeyman?" Blair interrupted. Dean pointed his fork at her.

"Don't make jokes. The boogeyman is dangerous." Blair just laughed.

"Why did he come out from under your bed and steal your sense of style?" She asked.

"Okay guys just listen. Here's where it gets weird." Sam continued. "All three victims were former football stars at the local high school. Each of them was wearing their letter jacket and they were all missing their feet."

"Their feet!" Dean said disgusted.

"Letter jackets!" Blair exclaimed disgusted. Sam just rolled his eyes.

_Four hours later._

"So, why did you want to get away?" Dean asked.

"I wanted to experience the joys of out dated rock music played in a car older then me that is driven by someone wearing a leather jacket." Blair answered.

"Funny. I'll have you know that this car is a classic. You agreed to the music when you got in the car. My jacket is cooler then you'll ever be." Dean replied. "But keep deflecting."

"I am not deflecting." Blair said, annoyed with him once again. "I am simply observing the world around me."

"Right. Try looking out the window princess. There's a whole big world out there. Most of which has no idea what an Elton Laldorf original is."

"Eleanor Waldorf!!!" Blair snapped. "An Eleanor Waldorf original. This skirt is worth more then your car."

"That's just sick." Dean said.

"Could you both shut up. Some of us want to sleep a little before we go after a demon with a foot fetish." Sam groaned from the backseat.

Dean and Blair quickly settled into silence.

_Hours later in Phoenix_

"So, what are we doing here Sammy?" Dean asked adjusting his tie. "FBI? Homeland Security? NSA?"

"Do you know that's illegal?" Blair asked him. "Impersonating a federal employee."

"Did you know that you could have fed half of the starving children in the world instead of buying that skirt?" Dean mocked her voice as he shot an insult back. Blair shot him a withering glance. "If looks could kill you'd be on the lam baby." Dean said.

"Don't call me baby." She said.

"Guys!" Sam said exasperated. "Okay, FBI. Blair is our forensic expert. Let's go."

They walked into the Phoenix city morgue and approached the man at the front desk.

"Excuse me. Agents Boucher and Tonkins, FBI. We're here to see the footless dead guy." Dean said flashing his badge at the man.

"Um. I'm sorry I'm not supposed to let anyone back there." The man said taking an authoritative stance. "Not only the chief examiner gets back from vacation."

"Did you hear me son. F. B. I. This is federal son." Dean said getting angry.

"Orders are orders, federal or not." The man said.

"Look, George I am gonna..." Dean was stopped by Blair moving between him and the scrawny medical man.

"I apologize for my colleague his life partner left him for a woman and he's a little broken up. Can we please just take a peak at the bodies. I promise we won't touch anything." Blair smiled sweetly at the man and placed her hand on his arm. "George." She batted her eyelashes and Dean almost threw up.

"Well, okay just don't touch anything." The man said leading them back. "He's under the sheet over there. Five minutes." The man disappeared and they moved towards the body.

"So, my life partner. Nice touch I'm glad to see that you see me as non threatening sexually sweetheart. Wanna share a bed at the motel?" Dean gave Blair a little smack on the ass and she spun around.

"It worked didn't it, tough guy." She slid towards him, laying a hand on his chest. "Will you protect me from the boogeyman?" Dean smiled at her, thinking his charm was working.

"Oh baby and so much more." He said. Blair pushed him backwards.

"Not even in your dreams perv." She said moving to where Sam was investigating the dead guy. Dean followed her annoyed but watching her hips sway none the less.

"Dean, it almost looks like the feet were pulled off of the legs." Sam said replacing the sheet. "That is definitely not something a human could do."

"Gross." Blair said wrinkling her nose at the smell of the dead man. "Look, he's got something tattooed on his ankle." She said pointing. "It looks like a star or something."

"Pentagram." Dean said. "Damn, satan lovers. Let's go Sammy I'm beat."

"What does that mean?" Blair asked.

"It means time for sleep, sweetheart." Dean said over his shoulder as Blair ran to catch up with them.

_At the motel._

"This is definitely not a three star hotel. I don't even think it's a one star." Blair said wrinkling her nose. "Why couldn't I have my own room?"

"I don't want you to get cold, princess." Dean said leaning back and turning on the tv. "Plus who's gonna clean up my socks." He said flinging his dirty socks on the floor in front of her.

"As if." Blair said moving to the other bed. "Fine, but I am not sleeping in the same bed as either of you."

"Wouldn't dream of it baby. I don't want to get my soul sucked out." Dean said taking a swig of his flask.

"What does that mean?" Blair asked glaring at him.

"One word, Suc-cu-bus." He replied.

"You wish." Blair said, not knowing what it was but assuming it was a sexual innuendo.

"Blair, it's fine I'll sleep on the pull out. Go ahead and take the bathroom first." Sam said interrupting their constant bickering. Blair smiled at him and went into the bathroom, slamming and locking the door behind her.

"Dean, can't you be nice?" Sam asked annoyed with his older brother. "She's obviously upset about something."

"Sammy that woman is evil. I think we need to get some salt or something from the trunk and check." Dean said moving to get the keys. "What normal person knows who made their damn clothes."

"Dean, she's from New York City. She's never been away from home without anyone she knows before. Something made her want to leave. Just give her a break. The skirt is nice." Sam said.

"Fine, whatever, but I'm sleeping with my gun." Dean said rolling over and turning out the lamp on the nightstand. Sam rolled his eyes and settled onto the pull out bed.

In the bathroom Blair wiped her eyes as the tears started to fall. _What the hell am I doing? _She thought. _Experiencing life._ She reminded herself, taking a deep shaky breath. _Chuck Bass can go to hell or get eaten by the boogeyman_. Blair smiled at the thought. She opened the door and slid in between the scratchy dirty sheets. Normally she would have whined and made them go with her to find some new ones at the management office but Blair was exhausted and she just didn't care anymore. Soon she fell asleep lulled by the sound of the snoring Winchesters on either side of her.


	2. Cherry Pie

Note: I changed the location of the story from Phoenix to the good old Midwest because Dean would be too hot in his leather jacket in the desert and I love Dean in a leather jacket!!!

Sorry it took so long to update, school and major writer's block.

I own nothing, etc.

Two Days Later

Blair still had no idea how they could eat this slop. The sign out front promised "Our food is so good you'll want to write home about it." This food was definitely not something that she wanted to write home about.

"Cupcake eat your breakfast before it gets cold." Dean said devouring his second stack of pancakes. Blair glared at him with her best bitch stare and he just continued to eat, with his mouth open, just to annoy her.

"I am not a cupcake." She shot back.

"Sorry you just look good enough to eat, I guess I could call you sweet cherry pie." He said thoughtfully. Blair looked confused and then kicked him under the table. She remembered some stupid old song he had played about that and it definitely was not about Blair Waldorf.

"Ow!" Dean yelped. "Look Cherry..."

"Do not call me that!" Blair yelled. "I am not swinging on anything!" At that Dean dissolved into uncontrollable laughter.

"Oh baby if I know my luck you will be soon enough. I'll have you swinging and then some." He winked at her and Blair fought the urge to slap him. He was more perverse then Chuck Bass and Blair did not let people speak to her that way.

"Sam, your brother is disgusting. I don't understand what went wrong." Blair said as Sam slid into the seat next to his brother.

"Dropped on his head multiple times." Sam replied quickly, laughing. "Don't worry it's just a conversation device. Otherwise all he would have to talk about is mullet rock and girls that don't want him."

"Funny Sammy. How about we talk about some demon lovin' and psycho powers so that you can join in." Sam instantly tensed but did not bother to reply. Blair simply looked back and forth between the two brothers, confused.

"Anyways, I got some information on the victim's families I think we should start with the first victim. Tim McShanty, his fiancee lives just down the street. They were together for five years. She would know something about the tattoo." Sam said flipping through his notebook.

"What are you going to do ask if he was a Satan worshipper?" Blair asked bluntly. "That seems a little tactless."

"Lucky for us Sammy and I have mountains of tact. I'm not just good looks and charm you know there's something upstairs too." Dean said smugly leaning back.

"Yeah, the lyrics of every mullet rock and lots of air." Sam said smiling at Blair who laughed while Dean tried to think of a retort.

"Whatever, you two just keep ganging up on me." Dean said annoyed. "Let's go dead guy's girlfriend awaits." Sam lead to way back to the Impala and Dean threw down some cash to cover the bill. Blair wiped her fingers with a wet nap from her purse and followed the boys out of the diner.

At dead guy's girlfriend's house

"Allison Marion?" Sam asked when a petite brunette answered the door.

"Yes, who are you?" The girl replied wiping her hands on the floral apron she was wearing.

"I'm Agent Colt and this is my partner Agent Mullet we're from the state police office." Sam pointed to Dean who tried hard to hide his annoyance. Blair cleared her throat to remind Sam she was there too. "Oh yes and our assistant Ms. Cherry." Blair leveled a glare at Sam and Dean tried hard not to laugh out loud.

"Come in, how can I help you Agent Colt?" Allison asked moving to let them enter. The house was sparsely decorated with a few pictures of Allison and Tim decorating the walls. Allison led them to the kitchen at the back of the house and gestured for them to sit at the rickety wooden table in the center of the room.

"We have a few more questions about Tim. I understand he was your fiance." Sam said sliding awkwardly into the low wooden chair.

"Yes, we were together all through high school." Allison looked visibly upset at the mention of Tim's name and fidgeted with her apron strings. "I still can't believe he's gone."

"We're very sorry for your loss ma'am." Dean said. "We just have a few questions." Allison nodded and Dean continued. "Was Tim involved in any spiritual organizations before his death?"

Allison looked confused at the question and appeared to be deep in thought.

"You know like Satan lovers or something." Blair blurted out sick of waiting for an answer because the kitchen smelled funny and the chair was giving her splinters in her ass. At this Allison's eyes went wide and she looked furious.

"Why would you say that! Tim was a good man! He may lost his scholarship but that wasn't his fault!" Allison stood up knocking her chair backwards. "The deal was only meant to last four years and his was up!" At this her eyes went wide and she quickly moved to the sink and began washing the dishes.

"What deal?" Dean asked.

"Nothing. I want you to leave now." Allison said "I have to get ready for work."

"Thank you for your time ma'am we're sorry if we caused you any distress." Sam said. He grabbed Blair's arm and practically dragged her outside.

"You're hurting me!" Blair cried once they were outside and Sam let her go roughly.

"What the hell were you thinking!?" He asked. "Tact?" Sam began to pace obviously angry.

"Seriously, Cherry Pie. What the hell? Now she's probably calling all the other families and none of them will even give us the time of day. So all we know is there was some kind of four year deal." Dean huffed over to the Impala and leaned against it.

"Sammy let's take Cherry here back to the motel and then see what we can find out on our own. Maybe they will be more welcoming without the loud mouth assistant."

"Do not call me Cherry!" Blair declared for what felt like the 100th time that day. Dean just shrugged and started the car.

Back at the motel

Blair was irate. They had unceremoniously dumped her at the door to their room and then driven off without even a backwards glance. No one treated Blair Waldorf like that. She opened her cell phone determined to call someone to come pick her up. She was over this little adventure.

With her finger poised over the power button Blair froze. She was sure that Chuck had one of his detectives attempting to find her right now and if she turned on her phone no doubt it would be traced. The last thing Blair wanted was Chuck Bass to show up and try to be her knight in shining armor. Although watching him beat up Dean for calling her Cherry Pie would be delicious she wasn't quite sure that Chuck would win. Dean probably fought dirty and Chuck was more about mental warfare then physical violence.

There was a sharp rap on the door and Blair's head snapped up. She wondered who on Earth would be knocking on the door of this seedy motel, unless it was the boys wanting to apologize and they had given her the only key. She set her phone down on the bed and moved to open the door. There was no peephole which Blair thought was a safety violation and planned to complain to the manager about as soon as Dean and Sam got back.

Blair opened the door slowly and recognized Chuck's private detective standing on the other side.

"What the hell do you want!" She asked angry that Chuck would have the audacity to send the detective to talk to her directly. Figures he would send a minion rather then coming himself.

"Miss Waldorf. Mr. Bass has asked that I find you and bring you back to the city immediately." The detective, whose name was Mike Blair thought. Made a move to open the door more but Blair held firm.

"I am not Mr. Bass' property he cannot simply demand my return. I can make my own decisions and I am saying." Blair said forcefully attempting to close the door.

"Unfortunately Miss Waldorf Mr. Bass gave very specific instructions and you are going to have to come with me." Mike said reaching for her and pushing the door the rest of the way open. Blair was pushed backwards by the force of the door opening.

"I will not go back to him until he gets off his high horse!" Blair yelled trying to fight Mike off. She was no match for him as he took her arm and pulled her towards the door.

"Get your hands off her!" Someone yelled from the doorway and before Blair knew what was happening a large pair of hands had grabbed her away from Mike and moved her to the other end of the room while a blur of leather punched him in the nose.

"I'm a detective under the employ of Charles Bass and he has asked me to bring Miss Waldorf back to the city." Mike said trying to block Dean's fists.

"Who? Why should I care?" Dean asked lifting the man to his feet. "Miss Waldorf is not a prisoner she can leave when she wants and obviously Mr. Fish or whoever is not reason enough for her to leave." Blair smiled at Dean butchering Chuck's name.

"I have my instructions." Mike replied indignantly.

"Well tell Mr. Fish you have new instructions courtesy of Agent Mullet." Blair smiled again. "Go back to the city and tell him to grow some balls. A real man doesn't send his lackey to bring back his lady love. He gets her himself." Dean threw Mike out the door.

"But Miss Waldorf." Mike started looking at Blair.

"Is perfectly safe." Dean started to close the door and stopped. "Oh and tell Mr. Fish head or whatever that Agent Mullet says that he obviously has no idea what a good thing is when he has it." With that Dean slammed the door and locked it.

"Are you okay?" Sam asked turning to Blair concerned. "Who is Charles Bass?" Dean moved closer and looked at Blair's arm where a slight purple bruise was starting to show.

"It's a long story..." Blair said

"We have time, Cherry." Dean said taking a seat on the couch. Blair sighed and started her story.

Later that day in New York City

"She's where! With who!" Chuck was irate. Mike had come back without Blair.

"Agent Mullet at least that's what he called himself." Mike said trying to avoid Chuck's angry glare and his penchant for throwing things.

"What is she doing with two strange men in a no star motel in the freaking middle of nowhere." Chuck squeezed the glass in his hand and Mike was afraid it was going to break.

"I don't know but Agent Mullet said that she was safe, isn't that all that matters?" Mike asked hoping that would at least calm his employer down.

"No, she doesn't belong with them. She needs to be here with me." Chuck shouted. He could not believe that she had done this, running out on him and disappearing with two mysterious men whose license plate couldn't be traced. Chuck was almost tempted to call the police but he knew Blair's parents would freak and this would only make her angrier.

"Look, Mr. Fi..Bass." Mike quickly corrected himself when Chuck's gaze snapped towards him. "They said that you should get her yourself maybe that's what she wants. She was pretty upset that you sent me."

Chuck simply nodded and started to think of ways to win this little game Blair was obviously playing with him. He mouth formed his trademark smirk and he hit speed dial three on his phone.

"Gloria, I'll need the jet in two days. I'm not sure yet. Yes, thank you." Chuck snapped the phone closed.

"Mike, back to the bread basket. Watch her make sure she's safe. I'll follow you in a couple days. I want her to see that Chuck Bass does not come when beckoned." Chuck smiled and Mike just shook his head. Sometimes he thought if Chuck spent less time trying to one up Blair and more time telling her how he felt that Mike's job would be a lot less frustrating.


	3. Black Betty

"So he called you to cancel plans and your response was to get out of the limo and hitchhike?" Dean was absolutely mystified by this strange girl whose tendency for overreaction was beyond belief.

"You don't understand. This is the third time we've had important plans and he's cancelled. The first we were supposed to fly to Italy he cancelled and slept with an interior designer. The second time we were going to have dinner after he disappeared and the next day I found him in his office with two half naked bimbos and some drugs while I had thrown him a brunch with the board of his father's company. This was the last straw." Blair was angry all over again remembering how Chuck had invited her to the Hamptons for the weekend so they could be alone and talk. Then when she was almost there he had called to say he had an emergency at the company and couldn't come. Blair had called Serena told her that she was going to the Hamptons and to tell her mother she was staying with Serena for the week. After that Blair had turned off the phone ordered the limo to stop and stuck her thumb out like they did in old movies. She was furious and knew disappearing from the highway would make Chuck furious. It served him right.

"So why do you keep going back to him?" Dean asked. "What's the draw if he keeps breaking your heart?"

"I love him." Blair said simply. Dean let out an exasperated sigh and moved over to the bed and turned on the tv.

"Sorry he's a bit cynical." Sam said. "Look I get why you're upset but was hitchhiking really a good idea? What if it hadn't been us that picked you up? Wouldn't a trip to the spa have been a better idea?" Blair smiled.

"You don't know Chuck Bass." She replied. "A spa weekend would barely make him twitch. Hitchhiking with handsome strangers that's gonna drive him wild." Sam just shook his head.

They heard a sharp rap on the door and Blair was suddenly scared that Mike had returned for her. Sam gestured for her to move by Dean and he went to open the door. Blair sidled next to Dean and saw both brothers tense as Sam turned the door knob.

"Ruby." Sam said with a sigh of relief opening the door and letting the dark haired girl in. Sam instantly relaxed but Dean tensed even more. Blair glanced at him and notice his jam was clamped so tight his muscle was twitching. She laid a hand on his arm and could feel his muscle rippling under the leather of his jacket.

"Who's that?" Blair whispered. She looked the other girl up and down and noted that she looked greasy and was attempting to look tough with her leather jacket. Sam seemed happy to see her but Dean obviously thought she was a threat.

"Sam's demon playmate." Blair's eyes widened at the mention of the word demon so Dean continued. "She claims to be a good demon, you know on our side and all. I don't trust her. Stay close." Blair moved closer and Dean shifted so she could sit next to him on the bed.

"Whose the princess? Dean's latest groupie?" Ruby asked stalking toward the two on the bed.

"This is Blair, she's helping us in the investigation." Sam said. Blair smiled her best ice queen smile at Ruby who smiled back but her eyes turned black. Dean saw what Ruby did and glared at her, wrapping a protective arm around Blair.

"Play nice demon girl. Blair's only going to call the fashion police not send you back right where you belong." Dean said. Ruby narrowed her eyes at him.

"Last I heard you weren't complaining about the accommodations downstairs. Maybe even enjoyed it a little?" Ruby shot back and Blair looked at Dean confused. He looked alive so she wondered what Ruby meant by him being downstairs.

"Guys!" Sam yelled, again annoyed by the banter between his friend and his brother. "Dean, Ruby and I have to go take care of something. Will you two be able to not kill each other while I'm gone?" Dean was not happy about the idea of Sam going off with Ruby but he was anxious to get rid of the demon so he didn't argue this time.

"I can handle myself. Cherry Pie here might have to contain her wild desire for me but otherwise we should be fine." Blair smacked him in the chest but didn't move away because she was still uneasy about the greasy demon girl standing not five feet from her.

"Cherry Pie?" Ruby asked. Sam just shook his head and they moved towards the door and left. Once the door clicked shut Blair shot off the bed and turned to glare at Dean.

"Cute mullet boy." She said, annoyed that he was still calling her Cherry Pie. Dean just shrugged he looked bothered by what had just happened and started flipping through the channels agitated. He got up and pulled a bottle of Jack Daniels from his bag. He took a swig from the bottle and started to pace the room.

"You are not about to get drunk." Blair said in her best Queen B voice. "I am not going to sit here with a drunken pervert." Dean glared at her but returned the bottle to his bag. Too annoyed with his younger brother to argue with her. Blair smiled at the small victory.

"What is it with that greasy demon anyways?" Blair asked Dean. "She smells like a biker bar and her clothes are seriously 2003." Dean laughed.

"Don't ask me I liked her better as a blonde." He said. Blair was confused thinking that Ruby would look weird would look strange with blonde hair. "Demons can take over people's bodies. Ruby's last meat suit, as she says, was a spunky hot blonde. I'd say she's moved down in the world." Blair's eyes got wide again.

"Meat suit?" She yelped. "What the hell is this? A demon is wearing her?" Blair was shaking.

"Sshh. It's okay." Dean said wrapping his arms around her protectively. "I'll protect you." For some reason hearing those words made Blair start crying. She cried because Chuck had hurt her again, she cried because she was scared. "Blair, I won't let anything happen. Come on let's go get something to eat. I'll buy you a milkshake." Blair just nodded and wiped her eyes. She followed him out of the room hoping the milkshake was made with non fat milk but knowing that it wouldn't be.

_Later after a milkshake_

"What are you doing?" Blair asked. Dean was glad she was back to her prissy self but annoyed none the less.

"Settling in for a long night's sleep." He replied flipping through the channels again.

"That's my bed." She announced, hands on her hips. Dean admired her form in the black nightgown she had changed into.

"Was your bed, Cherry. My back hurts from my knight in shining armor rescue this afternoon and this mattress is more supportive." He said settling into the pillows.

"But I have a delicate back. I need the extra support." She whined.

"There's room Sweetcheeks." He said patting the bed next to him and admiring her ass as she bent to put her toiletries bag back in her suitcase.

"Don't call me Sweetcheeks!" She yelled tossing her headband at him. "I am not sharing a bed with you. You would probably think that meant I wanted you, which I do not."

"That's your loss because this" Dean gestured at his body pausing noticeably by his crotch. "Is definitely worth the wait. It's been said that I make dreams come true." Blair rolled her eyes.

"Fine. I'll prove to you I don't want you." She took the pillows off the other bed and make barrier between them. She crawled under the covers and settled on her side, facing away from Dean.

"Oh baby don't challenge me. Although we'll both win in the end." He winked at her and turned off the T.V. Blair rolled her eyes. At least Chuck was a master of the double entendre, Dean was much more blunt.

_Later_

Sam slipped in quietly not wanting to wake them. He was sure Dean had a lecture all prepared and Blair was probably scared to death. Sam paused after shutting the door and waited to here Dean start yelling. All that greeted him was the sound of Dean snoring and Blair's soft breathing.

He flipped the light switch and was amazed to see Dean and Blair snuggled together on one bed. Dean had his arm around her and she was curled against him. Sam shook his head. Grabbed his pillows off the floor and laid on the other bed, falling asleep instantly.

_The next morning_

Blair woke slowly. She could hear someone's heart beating in her ear and a strong arm was holding her close. She breathed in deep expecting it smell a mixture of high end Scotch, smoke, and expensive cologne. Instead she was greeted with the scent of sweat, leather, Jack Daniels, and something she could only describe as musk. She instantly sat up and wrapped the sheets around her.

"Dean! What happened to the pillows?" She screeched. Dean blinked awake and looked at her.

"You curled up next to me. See I told you that you couldn't resist." He smirked at her at some point he had shed his shirt and Blair couldn't help but admire his well muscled chest and arms. Then her gaze shifted lower and she moved off the bed, appalled.

"What is that? You are disgusting!" She tightened the blankets around her which only served to pull them off Dean and reveal he was only wearing his boxer briefs and his rather large morning wood.

"Cherry don't flatter yourself. It's morning, naturally happens." Dean said. "However if you like what you see we could arrange something." He winked and Blair dropped the blankets, storming off to the bathroom.

"Dude, why can't you just be normal?" Sam asked rolling over and running a hand through his hair.

"Don't get me started on you Sammy." Dean said pulling on his jeans and the nearest t-shirt. "We're gonna talk about last night. Don't think for a second we're not."

"Whatever Dad." Sam said getting up and turning on the coffee maker.

"Dad would have already beat your ass." Dean replied. Sam rolled his eyes. It was obviously going to be a long day.


	4. One Dance

**Note: Thank you so much to everyone who reviewed. They are what fuel my fire, well that and Dean;) . Everyone's excitement for the inevitable Dean/Chuck smack down makes me really nervous to write it but definitely in a really good way. However that will have to wait for another chapter, just to keep the anticipation high! Also new episode of Supernatural yesterday and new Gossip Girl Monday have me in a haze of excitement.**

_After several hours spent interviewing the victim's families_

"That was waste." Dean said leaning against the Impala and sipping from his flask.

"I think it's safe to say that Allison shared her little experience with Colt, Mullet, and Cherry with the whole town." Sam said sighing. "This case is getting more frustrating. What's our next move?"

"Let's go see how Blair's doing at the library." Dean decided. They had made her go to the library to read up on the victims rather then risk her pissing off more bereaved family members. Sam nodded and slid into the car next to Dean.

_At the Library_

Blair was getting a headache from starting at a computer screen for the last, what felt like, 15 hours. It turned out the four victims were pretty popular with the Small Town Midwest Chronicle and she had read every article and took notes. She wasn't Constance's best student for nothing.

"Hey." Dean whispered coming up next to her. Blair quickly put her hand up to silence him. She had one more article to read and she didn't want to be interrupted.

"Hang on, I've got one more article to read. Go find a quiet table somewhere and I'll fill you in after I finish this." Dean scowled but he lead Sam over to a table in the corner.

Blair finished reading her article and signed out on the computer log. She slid into a chair across from the Winchester boys and smiled at them. Dean figured she had just purchased some new $1,000 junk online he recognized smile of triumph when he saw it.

"So, what do we have?" Sam asked. "Interviews were a bust so we really need something here." He kept running his hands through his hair, like he was nervous or on edge. Blair's smile grew.

"Well it's your lucky day." Blair said triumphantly. Dean rolled his eyes but leaned in expectantly. "Let's start with the simple stuff then I'll get to the cherry on top." At the word cherry she looked at Dean and he chuckled.

"So, you like to be on top?" He asked. "Sounds good to me." Blair glared and kicked him under the table.

"Dean, could you contain your perverse thoughts for like ten minutes?" Sam asked exasperated. He was losing patience quickly and would rather not get in a brawl in the middle of a Library. Dean mumbled something that sounded like "What crawled up your ass?" but he shut up and motioned for Blair to continue.

"So all of our victims were football players for the high school team. They were known as the Ferocious Five. They lead the team to four state championships. Local heros all had full rides to state schools." Blair turned the page and Dean wondered what this had to do with anything and why she was so excited.

"They all lost their scholarships after one season. It seems their talent went missing as soon as they stepped onto the field. Fumbled the ball, couldn't catch, kicking only 10 yards and so on." She took a deep breath. "Thus they all returned home and next thing you know wound up dead."

"Wait. You said five?" Dean interrupted. "There were only four corpses. Did we miss one?" Blair pursed her lips in frustration.

"If you would just let me finish you would understand." She said shortly. "Now, according to the papers all the corpses were missing their feet. However, the autopsies show something entirely different." Dean raised his eyebrows but kept him mouth shut for once. "It turns out that Tim was the only one lacking his feet. Tommy was missing an arm, Ron his hands, and Devon his entire right leg."

"So the police lied to smoke out the killer?" Sam asked. "What's the significance of them all missing different body parts?" Blair's triumphant smile returned again.

"Well Tommy was the star quarterback, Ron was the running back who never missed a pass, Tim was the fullback who ran like the wind, and Devon made a 48 yard field goal." Blair continued to smile not only at her ability to uncover this little detail but also because she knew what these positions were.

"So you're saying that these boys were football prodigies who lost their magic appendage?" Dean asked. "That's a little messed up." Blair nodded her agreement. "So you're a big football fan? New York Giants in their tight pants get you going?"

"Actually, I prefer the Yale Bulldogs. My father takes me to a game once a year. It's not hard to pick things up from the 50 yard line halfway up." Blair smiled at him. "Anyways, it turns out that there is one more member of their little gifted group. Johnny Malone, he was the defensive end."

"The next victim?" Sam asked. "Wait, how did you find out about which limb they were really missing?"

"I know a thing or two about hacking. Just something I picked up." Blair said flipping back her brown curls. The truth was that she and Chuck had hacked some e-mails once in order to ruin some little freshman who was going around telling everyone that she had slept with Nate. "So, I think we need to find this Johnny and figure out what's going on."

"Agreed." Dean said. "But first I need some grub. I think I'm in the mood for Cherry Pie." With that he turned his gaze on Blair looking her up and down. She used her notebook to cover herself and brushed past him. "Oh baby I hate to see you go but I love watching you walk away." He called after her. Blair quickened her pace.

"You got a burger to go with that shake?" Dean yelled across the Library eliciting smirks and glares from the other people. Blair practically ran out the door in embarrassment. Sam just shook his head and pushed his brother along before they were forcibly removed from yet another Library because Dean couldn't keep his mouth shut.

_Later that night_

"So this is where our next victim lives?" Blair asked eyeing the rather large Colonial house. "It's the nicest house I've seen in this whole in the wall town."

"His father is the mayor and they own a construction company." Sam said, he had googled Johnny Malone earlier. "That's his truck out front. So he has to be home." Suddenly a figure emerged from the side of the house and they all strained to see who or what it was.

"It's Johnny." Blair whispered.

"How do you know?" Dean asked.

"I saw his picture when I was researching. Plus his name is on his letter jacket." She said pointing at the distinct jacket he wore. Johnny slid into his truck and sped off. Dean quickly threw the Impala into gear and followed him.

Johnny drove recklessly through town and out towards the nature reserve outside of town. He slammed his brakes as he flew into a parking spot and disappeared into the trees.

"Sammy get some ammo we gotta follow this son of a bitch." Dean said getting out of the car.

"Dean by the time we get everything together we'll have lost him and it's too dangerous to go in there unarmed. Let's come back in the morning and see what we can find." Sam said.

"Fine, but if he ends up dead it's on your head." Dean said reversing the Impala out of the parking lot and speeding towards the motel.

_The Next Morning_

"There was fire here." Sam said running his fingers through the ashes. "More satanic symbols on the trees. Definitely not your garden variety late night activities."

"What do you suppose he was doing?" Blair asked.

"Ritual of some kind. Probably praying to some nasty thing to save him. He has to know he's next if all his buddies are already six feet under." Dean said. "What's the connection?"

"Football." Blair said simply. "They were heroes. Talented, won every game, never missed a pass, block, kick, whatever. Then it stopped. As soon as they went to college." Dean and Sam nodded.

"Can't be the field or everyone in this town would be the next Tom Brady or Barry Sanders." Dean said thinking hard.

"They made a deal." Sam said. "Four years of talent. That's why whatever is killing them takes their legs, feet, arm, hands because those parts were what gave them the talent. The demon wants them back."

"Then why kill them?" Blair asked. "Why not just take the magic parts?"

"Demons are sick puppies." Dean said. "Who knows, maybe they bled to death, heart attacks. Demons aren't ones to make sense." He stood up and wiped his hands on his jeans. "Looks like we need to find a demon that can bestow talent. I'll call Bobby see what he knows." Dean pulled out his phone and walked away to make his call.

"Who's Bobby?" Blair asked.

"A friend." Sam said simply.

"A demon friend?" Blair asked cautiously. Sam's head shot up.

"No, more like a surrogate father." Sam said. Blair let out a sigh she didn't think she wanted to know anymore of the Winchester's demon friends.

"Bobby's gonna look. He says he remembers something from another case he worked a while back." Dean said rejoining them. "Let's get outta here. I'm hungry." Blair rolled her eyes it was beyond comprehension how he was always so hungry.

_Later_

Ruby had called and Sam left again. Blair and Dean had been sitting in the motel room waiting for Bobby to call back but something was obviously bothering Dean.

"Would you just sit down? You're making me dizzy." Blair said, annoyed because Dean was pacing the room again.

"I don't like that chick. I don't care if she did save his life or whatever. I don't like her." He had been repeating this like a mantra for several hours now.

"Dean, calm down. Sam's a big boy he can take care of himself." Blair settled back to enjoy the movie she was watching.

"You wouldn't understand you don't have any siblings." Dean shot back. "My dad told me to watch over Sammy."

"I get it." Blair said simply. "I have a friend who was always a big mess and I was always the one holding back her hair or looking for her in bathrooms. It's an instinct." Dean nodded in agreement. "You have to just relax. At some point letting them go is all you can do." They sounded like empty nesters talking about their children.

"You want to go get a drink?" Dean asked fidgeting again.

"You do know that I'm only 18 right?" Blair asked.

"Young and impressionable just how I like em." Dean said and for once Blair didn't smack him. She was just glad he wasn't pacing anymore. "Don't worry. A little T and A goes a long way." Blair rolled her eyes again.

"Just give me a minute to change." She said pulling out a few dresses and walking to the bathroom. Dean gave his shirt a quick sniff and figured it was probably time to change it.

Five minutes later

"Damn!" That was all Dean could manage when Blair emerged from the bathroom. She was wearing the dress from her dinner with Chuck that he had cancelled. It was a little revealing for the bar but Dean had asked for a little T and A. Plus she was hoping he would shut up about Sam.

"You said T and A." Blair said.

"That'll work." Dean said admiring her long legs and rather ample breasts. "Mr. Fish really is a complete and total moron." Blair blushed at the compliment.

"Shall we?" She asked. Dean nodded offering her his arm but not taking his eyes off her rack.

"Cherry, I need your mother's address I want to thank her for everything that she gave you." Dean said sneaking a peek at her ass.

"That might be interesting." Blair said sliding into the passenger seat of the Impala.

At the bar

After several drinks, most sent to Blair by other patrons, Dean decided that it was time for a song. He left Blair with yet fifth free drink and moved to see if the jukebox was going to make his dreams come true. Dean chuckled to himself as he chose the perfect song and motioned to Blair to join him on the dance floor.

"What did you pick? AC/DC? I Love my Mullet?" She asked coming over and he took her in his arms.

"You'll see." He replied smiling as the song began.

_She's my cherry pie._

_Cool drink of water._

_Such a sweet surprise._

_Tastes so good make a grown man cry._

_Sweet Cherry Pie._

Blair's eyes widened as she realized the song he had chosen.

"Do you taste so good make a grown man cry Cherry?" Dean whispered in her ear. "Or is Mr. Fish not an eater?" Blair blushed but the alcohol was making her bold that and the way Dean smelled and the feel of his muscles through his T-shirt.

"Maybe you'll have to let me know." She whispered back, throatily. Dean felt his self getting harder and pulled her closer.

_Cause she wanted me to feed her._

_So I mixed up the batter_

_And she licked the beater._

"Will you let me lick the beater?" Blair asked sliding her hands down to his belt buckle. Dean groaned quietly in the back of his throat.

"Cherry I'll let you lick it twice." He whispered back. She smiled suggestively at him. Dean couldn't take it anymore so he just gave in.

Blair gasped a little when Dean's lips met hers. They were so different from Chuck's. They weren't as soft and his kiss was rougher, harder. She could feel his stubble scratching her cheek.

"What do you say we go back to the motel?" Dean asked breaking the kiss.

**Note: Lyrics are from Warrant's "Sweet Cherry Pie". I know the chapter was a little slow but I needed to move the whole case plot along. Read and review!!!!**


	5. A Visitor

They burst into the motel room barely bothering to close the door before Blair's dress is over her head and Dean's shirt soon follows. He lifts her up and she wraps her legs around his waist as he presses her against the door. The heat between them is intense and evidenced by the dampness of her panties and his burgeoning erection.

"Dean." Blair moans as he finds _that _shot on her neck.

"Blair, you are so incredibly hot." He whispers.

She muses how his sexy talk is so different from Nate's or Chuck's. Nate tends to mumble little I love yous and oh baby. Chuck is dirty, every other word is fuck or you like this. Dean is simple, direct and she likes it.

He flicks a finger between her back and the door and off goes her bra. He takes one of her nipples into his mouth and Blair leans back, pressing her hips against him, and moaning. He moves to the other one and her head starts to spin. Blair slides her hand into his pants and runs her hand up and down his rather large erection. She feels his sharp intake of breath against her chest as she strokes his length.

"Well Cherry. I knew you were a naughty girl underneath that haughty exterior." Dean whispers into her ear. Blair licks her lips in response but before they can continue they are interrupted by a knock at the door. They both freeze and the knock gets louder.

"Blair, I know you're in there." Comes the voice from the other side and Blair rolls her eyes. She grabs Dean's T-shirt from the floor and slides down against Dean's body until her feet hit the floor.

"Serena. How opportune." Blair sneers sarcastically. "Doing Chuck's dirty work I see." Her best friend pushes her way into the room and surveys the scene. Blair is dressed in nothing but an oversized T-shirt and her La Perla's. Dean is shirtless and his jeans are unbuckled. The evidence of why rather obviously hanging out.

"Blair, I was worried. You disappeared and I haven't heard from you. Obviously though you've been busy." Serena said gesturing at Dean.

"Um, obviously you two have a lot to talk about so I'm going to go take a cold, very cold shower." Dean said escaping to the bathroom as fast as he can.

"He's..rugged." Serena stated haughtily.

"At least he's not from Brooklyn." Blair shot back. Serena cringed but ignored the shot at her ex-boyfriend.

"Look Blair. Chuck may have told me where you were but I came here because I was worried about my best friend." Serena reached out and touched Blair's shoulder. "Cyrus and Eleanor are worried too. So why don't you come home with me."

Blair contemplated that for a minute. It was true that she had neglected to tell anyone else about her whereabouts and Dorota must be worried sick. Cyrus too. However, she had an itch that needed to be scratched and that was a more pressing concern.

"S, I'm glad you came but this is what I needed. Tell everyone I'm fine I'll be back soon." Blair started to move towards the bathroom but turned around before she reached the door. "And tell Chuck that he can go to hell for all I care." With that she opened the bathroom door and slipped inside. Serena shook her head and left the room.

She slid into the back of the waiting town car. Amazed yet again that Chuck had managed to find a car service in the middle of nowhere.

"She's not coming. She won't listen to me. She said you can go to hell." She told Chuck.

"Well the Midwest is close enough." Chuck replied. "Driver back to the hotel. I'll deal with Blair tomorrow." Serena decided it was best not to mention that she had caught Blair practically having sex with some hot rugged farm boy. There were just some things that Chuck Bass didn't need to know.

_Meanwhile _

Blair slipped back into the bathroom and heard the shower running. Dean's boxers and jeans were in a pile by the sink and Blair quickly shed the rest of her clothes. She slipped into the shower behind Dean and he turned around when he heard the rustle of the plastic curtain.

"Blair? What?" That was all he could get out before she had attacked him with her mouth. He once again lifted her up and she wrapped her legs around his waist. Dean pressed her against the wall and slid his hand down to her hot center.

He cupped her and Blair moaned against his mouth. With his thumb he began to trace slow circles around her clit. Blair could feel the pressure building and pressed her hips into his hand. Dean knew he wouldn't be able to resist her much longer after feeling how wet she was.

"Dean, fuck me." Blair whispered and it was all the invitation he needed. He slowly entered her, testing, before he plunged into her balls deep. Blair cried out with the intense pleasure that rushed over her. He continued to pound into her, seeking his release.

Blair slid her hand between them and touched herself. Matching his rhythm until she felt release. Dean followed soon after.

"That was amazing." He whispered sliding her down the length of his body.

Blair stepped into the shower and let the water wash over her. Dean soaped up his hands and ran them over her body, marveling at the soft curves. She returned the favor tracing his defined chest and well muscled arms.

They dried of and collapsed into bed. She put on one of his T-shirts and curled against his chest. Blair smiled contented. Dean wrapped an arm around her small frame and drifted off to a peaceful sleep. When Sam arrived hours later he noticed the clothing strewn about and noted the contented smiles.

"Well at least they finally just got it over with." He mused.


	6. Morning After

Blair woke up the next morning and smiled at the sleeping form next to her. Dean was snoring softly with his face half buried in the pillow. Her calm was instantly replaced with dread. She didn't know what to say when Dean woke up. Should she act like last night didn't happen? Act like it did? What was she going to do about Serena? Too many questions that all seemed to be attacking her at once.

Then it happened. Dean woke up and Blair tried to hide under the covers but she wasn't fast enough.

"Hey, Cherry." Dean whispered, pulling the covers away from her face. "Fun night, huh?" Blair couldn't help but blush.

"It was." She smiled at him and he moved to get up. "Dean, look I..." She started but he held up a hand to silence her.

"Cherry, you don't have to give me the speech. I'm not that kind of girl, blah blah. It was a one time thing, blah blah. I've heard them all and given them all." He paused. "Except the I'm not that kind of girl that would be a little weird. Anyways, no worries it was what it was."

"I'm not saying it wasn't great." Blair said trying to make sure he wasn't offended.

"Oh, baby I know it was great." Dean said winking at her and going into the bathroom. Sam groaned in protest from the other bed and Blair giggled.

_Later_

"So, when do you suppose your friend will be back?" Dean asked as they ate breakfast. "She seemed determined and you know maybe she liked what she saw last night and wants in."

"Ugh. In your dreams mullet man." Blair replied. Dean opened his mouth to say something but the waitress chose that moment to come back and he didn't want to give her a heart attack.

"More coffee?" The waitress asked. Dean and Blair both shook their heads and she disappeared.

"So, about that threesome?" Dean said pausing mid-bite to leer at Blair. Blair just rolled her eyes and ate her fruit plate. She was sure Serena would be back and probably with a suit wearing, scheming partner in crime.

**A/N: Okay so I need so input. I don't know where to go next, I can't decide between Blair ending up with Chuck and her ending up with Dean. I keep going back and forth. I love C/B (of course) but Dean/B seems to work too. So, let me know what you think and I'll make a decision on which way I want to go. Either way there will be a Chuck v. Dean showdown soon!**


	7. Demon Linebacker

A/N: Thank you to everyone who reviewed and answered my query. It really helped me to figure out where I want to go with this. Sorry for another short chapter but I had to break the rest up into the right bits or it wouldn't work.

I have finished the last chapters (about three more to go!) and will hopefully have an update by tomorrow if all goes well!!!!

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She was kneeling on the ground, in a forest. Blair Cornelia Waldorf, Queen Bee of the Upper East Side, was kneeling in dirt in a forest and she didn't mind. She figured that probably had something to do with the man kneeling next to her. The one she had slept with barely 24 hours ago, the one she was seriously considering luring to the back seat of the Impala for a repeat performance. She couldn't help it she had a thing for the back seats of motor vehicles.

"What are we waiting for?" Blair whispered. She shifted closer to Dean breathing in his scent. Jack Daniels, leather, and pure musk it sent shivers down her spine.

"He's summoning the demon. We're going to wait until it's here and then take care of it." Sam told her as he watched Johnny intently.

"What the hell is that?" Blair asked as something began to emerge from the flames. She opened her mouth to scream. Dean reacted quickly pulling her down to the ground and covering her mouth.

"They can't know that we're here." He said. Blair was enjoying the feeling of him on top of her again so she pretended to be contemplating another scream so he would stay where he was.

"Dean, we have to move it's getting heated." Sam whispered urgently. Dean nodded and gave Blair a look of warning. She closed her mouth and he removed his hand and pulled her up with him.

"Here, take these." He handed Blair the keys to the Impala. "If anything happens take it and get out of here. It's yours." He moved to join Sam but he paused and turned back to pulled her into a bruising kiss that left her legs shaky and her knees weak. Before she could recover he had rushed into the clearing close behind his brother.

Blair crept back behind the tree and watched. The demon was "wearing" what looked to be an NFL linebacker. His shoulders were broad and his arms were the size of Dean's thigh. Dean and Sam yelled at Johnny to run, which he did, without even looking back. Being that he had made the mess Blair thought he should at least have to stay and help clean it up.

While Dean tried to fight the angry demon into submission Sam kept attempting to do some creepy mojo thing with his hand which was clearly not working. There was sweat dripping down Sam's brow and he finally gave up. He yelled something to Dean who pulled a rather threatening looking knife out of his jacket and charged the demon. The monster shoved him hard and Dean landed with a thud on the ground.

After a minute Dean hadn't moved and Blair was getting worried and she was sick of being on the sidelines.

"Dean!" She screamed running out from behind the trees. The demon linebacker leered and ran towards her.

"Blair!" I told you to stay back there!" Dean said between moans from his spot on the ground. Blair screamed as the monster ran towards her. Sam tried to stop him but he wasn't fast enough. Blair turned and started running towards the woods.

"Sam! Help her! I'm right behind you!" Dean said trying to get up as fast as he could but his head was pounding and he kept stumbling. Sam took off after the screaming girl and the demon linebacker.

Blair felt branches tearing at her skin and clothes but she didn't stop. She didn't even bother to look back. She said a little thank you prayer that she had worn sensible shoes today and hoped that her semester of field hockey would pay off. She weaved her way in and out of the trees, trying to put some distance between her and the smelly thing chasing her.

Suddenly her path was blocked by something solid and she thudded to the ground as she slammed against it. She was temporarily disoriented but she could hear Dean yelling something. She looked behind her and saw Dean slam the knife into the back of the linebacker. It seemed as if once the knife sliced into him he was burning up from the inside as he screamed in pain. Then the meat suit fell to the ground and it was over.

Blair turned her head forward to see what she had run into. Her eyes went wide with surprise. "Chuck? What the hell are you doing here?" Blair asked haughtily.

"I could ask you the same but I'm a little distracted by those black panties you've got on display." Chuck replied leering. Blair quickly pushed her skirt back down and stood up. Dean came over, steading her and wrapping a protective arm around her waist.

"Who are you?" Dean demanded, his eyes were narrow and he pushed Blair behind him to protect her.

"I'm Chuck Bass." The dark haired man replied with a smirk matching Dean's threatening stare with one of his own.


	8. A Meeting in the Forest

A/N: I don't know how happy I am with this chapter. It was really hard to write because for some reason Chuck escapes me. He is the hardest character for me to write.

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"I'm Chuck Bass." Dean smirked. _So this was the infamous Chuck Bass_. He thought. _Interesting. _

"Mr. Fish we meet at last." Dean replied. "To what do I owe the pleasure?" Dean knew full well why Chuck was here he just wanted to push his buttons.

"That's my girlfriend standing behind you." Chuck motioned at Blair who was standing definitely behind Dean. Glaring at him.

"We broke up Basshole!" Blair shouted back.

"No, you decided to get out of my limo and hitchhike to this middle class dump. We never actually broke up."

"Well maybe me deciding to depend on the kindness of strangers instead of spending another minute with you should have been a clue." Blair was giving him one of her deadly stares now but Chuck was unfazed.

"A real gentleman would respect the wishes of a lady." Dean said stepping between the two. He had no idea where that had come from, sounded like something from an old movie he used to watch on tv when his dad went out hunting.

"A real gentleman wouldn't be wearing leather and driving a 40 year old car." Chuck said with a gesture towards Dean's jacket.

"Do. Not. Insult. My. Car." Dean said menacingly. Chuck smirked realizing he had struck a nerve.

"You mean your clunker."

"Nice purple suit is that how you attract your _special_ friends? Was Blair just a cover?"

"Purple signifies royalty and class, something you obviously know nothing about." Dean laughed.

"You mean stuffed shirts and puffy collars? No thanks." Chuck snorted and Blair giggled at the idea of the two of them dressed up like the people on _The Tudors_. She would be Anne Boleyn...Blair was snapped out of her thoughts by Dean nudging her.

"Fish over here wants to know whether you're going home with him." Dean said.

"Bass." Chuck snarled getting annoyed about being addressed as a slimy sea creature.

"Whatever." Dean replied looking at Blair imploringly. "So, what'll it be Cherry?"

"What did you call her?" Chuck asked, outraged.

"Cherry, you know like the fruit or the pie. Perhaps a flavor of soda pop." Dean snarked back at him.

"I know what the fuck a Cherry is."

"Do they have cherries under the sea Fish?"

"Bass!"

"Is that you're favorite kind of fish?"

"If you are too undereducated to understand a four letter word I'll be happy to spell if for you."

"That won't be necessary it rhymes with Cherry's most luscious body part." Chuck's eyes narrowed even more and he balled his hands into fists. Dean smirked because he knew that he had pushed a button. "Although her upper half isn't so bad either." That was the last straw.

Chuck's fist flew into Dean's jaw before he could react and it made a sharp crack. Sam tensed, Blair gasped, Chuck smiled, and Dean flew towards the smaller man.

"I should have figured you to be a sucker puncher." Dean said as he punched him square in the gut. Chuck doubled over in pain but his foot connected with Dean's shit causing him to curse loudly.

"Stop it!" Blair said moving in between them as they circled one another.

"What two guys fighting over you isn't your thing anymore?" Chuck spat out mad that she hadn't chosen him over the leather wearing hot head.

"Grow up Mother Chucker!"

"Why don't you? Your theatrics are what caused this in the first place!" Chuck was raging mad now. "You got out of the limo and decided to disappear! Do you know how worried I was?"

Dean wrapped a protective arm around Blair. "Hey, why don't you chill out?" He asked and Chuck simply glared at him.

"I'm staying at the Best Western, the suite. If you come to your senses I'll be there until tomorrow morning." With that Chuck was gone. Blair let out a hiss.

"Well he was almost as charming as his henchman." Dean deadpanned rubbing his now throbbing jaw and trying to ignore the pain in his shin.

"Chuck is a little jealous and overprotective at times." Blair told him turning to look at the purple bruise forming on Dean's jaw.

"You don't say."

Blair nodded. They stood in silence for a moment before Dean turned towards her and asked earnestly. "So what's it going to be Cherry?" She looked up to meet his eyes. They were boring into hers and he almost seemed worried about her answer.

"I don't know."


	9. Time to Think

Blair had been sitting in the diner for what felt like hours. She was sure she wouldn't be able to sleep so the Winchesters had dropped her off her. She needed to think.

Knowing Chuck Bass like she did Blair was sure that his offer to come home would only last until the next morning. If she did return home after that he would freeze her out. It was now or never. The last few months after Chuck had finally (bolded and underlined for emphasis finally) admitted his feelings had been amazing. But after everything that had happened with Dean Blair wasn't sure if Chuck was what she wanted anymore.

"More coffee darling? Looks like you have something on your mind. Boy trouble?" The waitress asked coming back. Her name tag said Dolores and normally Blair would have scared her off with a glare but she was tired and her head hurt.

"How did you know?" She asked Dolores and the older woman smiled knowingly.

"It's the look dear. A little piece of advice from an old lady. Sometimes the harder the decision the more life changing the answer." With that Dolores disappeared, leaving Blair to her thoughts.

Blair closed her eyes and pictured the two men. Chuck was refined, wealthy, suave like James Bond. She could picture their life together. An Upper East Side wedding. He would run Bass Industries, she would take over Waldorf Designs. They would have beautiful well-behaved children and attend all the society functions. It would be her fairy tale come to life, all be it with a different leading man then she originally imagined.

Dean was sharp, guarded, and tough like Indiana Jones. Life with Dean was a question mark. He and Sam were hunters, nomads. Her home would be a car and the things that went bump in the night would be her job. Would the job ever end? Would they ever be normal? The better question was would giving up her fairy tale be worth the question mark that would become her future. Blair sighed and wondered what someone else would do. The answers were easy and she made a mental list.

Dean - Serena, Jenny, Lily, Vanessa, Roman. Each of them would jump with abandon into the promise of adventure and never look back.

Chuck - Nate, Dan, Eleanor, Harold, Dorota. He was the safe choice (imagine that Chuck Bass the safe one). He was expected.

Cyrus was the real tiebreaker. He liked Chuck but Dean would no doubt win him over. It was impossible to know. Blair bit her lip and twirled her ruby ring as she thought.

_Half an hour later_

"Need anything darling?" Dolores asked breaking Blair out of her thoughts.

"Yes, do you have paper and a pen?" Dolores nodded and moved to grab what Blair asked for. "And some pie." Dolores smiled and nodded. She brought the paper and pen and Blair got to work.


	10. A Decision Made

Blair knocked tentatively on the door of Chuck's suite. Her stomach was in knots and she took a deep breath when she heard the dead bolt slide open.

"Waldorf, or should I say Cherry, what a pleasure." He said smirking triumphantly.

"I came to say good bye." Blair said curtly. "I thought I at least owed you that." Chuck's mouth fell open in shock. Blair smiled knowing she had caught him off guard.

"So you chose the leather head." He practically snarled. "What can he give you that I can't? The promise of Wal Mart shopping sprees and cheap material. We both know that isn't you."

"I want to see where this takes me." Blair replied. "I'll always love you Chuck but I have to do this for me."

"If you need to go get the pleather out of your system that's your problem. Just don't expect me to be waiting when you realize your mistake." He spat his eyes showing the pain he was in.

"I don't." Blair slowly kissed his cheek. "I love you." She turned and moved towards the door.

Once the door clicked shut Chuck whispered "I love you too." and let a single tear fall down his cheek. He grabbed his phone and barked into it. He was leaving now, he would not spend another minute in this podunk Midwest town.

Blair knocked on Serena's door and waited for her to answer. "B? Chuck just called you're not going back?" Her best friend asked answering the door and rubbing her eyes.

"I need to see where this will take me." Blair replied, pulling a stack of envelopes out of her purse. "Can you do me a favor S? Mail these for me. They're for my parents and step-parents. I love you S." Blair hugged her best friend tightly and turned to leave.

"One more favor." Serena nodded. "Take care of Chuck for me."

"I will I promise."

"Thank you." Blair smiled at her and slid out the door. She took another deep breath and moved towards the elevator. She could imagine the scandal. Blair Waldorf abandons the Upper East Side for poor demon hunter with multiple felony charges who has been reported dead by the authorities. Blair smiled, she always loved a good scandal.

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"So, you like her don't you." Sam asked his brother as they sat on a fence outside of town.

"She's something." Dean replied. "Fire and ice."

"Leather and lace." Sam added chuckling as he remembered Chuck's comments about Dean's wardrobe choices.

"She just got under my skin you know. A girl like that you don't want to lose. Once in a lifetime." Dean stared off into space.

"You sound like Dad when he talked about Mom." Sam whispered quietly.

"I think I might feel like Dad felt about Mom." His brother replied just as softly running a hand through his hair and trying not to think about how much he would miss Blair if she left.

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The door to their motel room was ajar. Both boys tensed and moved cautiously towards the door, hoping that is was only Cas and not Lilith or worse Alistair. Dean entered first and stopped in his tracks. There was Blair sitting on the edge of the bed smiling at him.

"Miss me Mullethead?" She asked. Dean couldn't help but grin at her.

"I thought you left. Dolores said you wrote a bunch of letters and disappeared. I was sure one would be under my door." Sam slowly slipped out of the room and closed the door.

"They were for my parents." Blair explained the smile on her face matching the one on his. "I thought they'd want to know I was okay and that I'd be traveling a lot now."

"Taking a vacation?" He asked still grinning.

"A road trip. Hunting things, saving people, a family business."

"I knew you couldn't resist my charms."

"It wasn't your charms that convinced me." Blair replied giggling as Dean swept her into his arms and kissed her deeply.

"I'm glad you decided to stay or rather go with us." He said resting his forehead against hers.

"Me too." Blair whispered back as they sank into the bed.


	11. The End

A/N: How cool am I? Four chapters in one night! This is the end. Thank you, thank you to everyone for the reviews, alerts, etc. It has made writing this slightly unconventional story a lot more fun!

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_One year later_

"What do you mean that I'm not allowed to interact with the victim's family?" Blair was outraged. "I have people skills you know."

"Yeah they were really obvious last time when the mother chased you out of her house with a frying pan." Dean replied Sam nodded silently.

"She was obviously experiencing some kind of stress disorder from her grief." Blair replied flippantly tossing her curls over her shoulder.

"Yes, obviously it was her fault that you called her son a Satan worshipping freak of nature." Dean rolled his eyes. "Either way you are relegated to research duty. Go use your people skills and get the librarian to show you the newspaper archives."

Blair scowled at him. "Fine! but you're not getting any for a month!" With that she stomped away towards the circulation desk.

"Fire and ice." Sam whispered laughing.

"Damn, Sammy look at that ass. She walks that way on purpose just to get back at me." Sam rolled his eyes and pulled his brother towards the Impala.

"Apparently that's all you'll be getting for a month."

"Please do you remember the last time she threatened a dry spell. I had her panting and begging within ten minutes." Dean smiled at the memory.

"Ugh, TMI." Sam told him as they went to meet the victim's family.

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_Two years later_

Chuck flipped through his mail. He had been in Tokyo for two weeks and the stack was rather large. A small ivory envelope with a familiar scrawl caught his eye. He slid a finger under the flap and pulled out a letter. Some photos fell out as he removed the letter and he placed them on the table as he began to read.

_Dear Chuck,_

_Serena says that you're happy and Bass Industries is making you billions. I hope it's true you know how she tends to lie and exaggerate to make people feel better. How is it having Cabbage Patch as an in-law and a stepbrother? Practically inbreeding if you ask me. Just wait till they have little Brooklyn babies that call you Uncle Chuckles. _Chuck was horrified at the idea of his sister procreating with Humphrey and made a mental note to tell her about the horrors of child birth in great detail.

_I saw a limo the other day and it made me think of you. _Chuck smiled at the memories that washed over him. _I wanted you to know I'm happy. I know that your stupid P.I. has been keeping tabs on me so you already know where we've been and what we've been doing. It's not easy but I really am happy. The Upper East Side feels like another world. _

_Anyways, I just wanted to tell you that Dean and I got married. We did it on the beach in California. Just me, Sam, Dean, and Castiel (Dean's friend from up North). I enclosed a picture for you. We're going to settle down in Maine. Dean's found a job up there and I might finally go to college. Cyrus offered to pay for it. I'm thinking about law school, arguing really is my strong suit. _

_Please be happy for me. We might stop in New York on the way to our new house so perhaps I'll see you. _

_Love, _

_Blair Winchester _

Chuck picked up the photos from the table. In the first one the bride and groom were smiling, deliriously happy, into the camera. Blair was wearing an ivory dress that was no doubt off the rack. She was beautiful just like he remembered. Her chocolate curls were blowing in the breeze. In the second Sam and the other man who must be Castiel had joined them. Dean was holding Blair in his arms and she was laughing.

He put the photos and the letter back into the envelope and tucked it into a drawer in his desk. He quickly grabbed his phone and hit speed dial. Serena told him that Blair and Dean would be arriving tomorrow and staying for three days. Chuck hung up without saying good bye and called his secretary.

"Evelyn, call the pilot I want to fly tonight."

"To where Mr. Bass?" She asked.

"Anywhere. Amsterdam sounds good. I need to leave tonight." With that he hung up. Seeing the newly married Mr. and Mrs. Winchester was not something he could stomach.

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_One year later_

"He's so handsome, Cherry." Dean said looking at the baby boy nestled against Blair's chest. She smiled contently and kissed the baby's head.

"Do you want to hold him?" She asked looking at her husband. He hesitated. "It'll be fine. I promise." Dean held out his arms and Blair placed the baby in them.

"He's so tiny."

"He looks like you." She told him and Dean studied the tiny creature. "He has your hair but my chin thank goodness."

"What's wrong with my chin?" Blair asked moving to feel her chin.

"Nothing mine is just more strong and manly. Good for a little boy." Blair rolled her eyes.

"As long as he gets my nose." She teased. "What do you want to name him?"

"I was thinking John Harold for his middle names." Dean said Blair smiled at the tribute to their fathers. "I don't know about the first name."

"He looks like a Cary." Blair said thinking of the dashing Cary Grant.

"Cary's a girl's name. He needs a strong manly name." Dean replied shaking his head. "What about Sebastian. You do love The Little Mermaid."

"Sebastian John Harold Winchester. I like it." Blair smiled. "I love you."

"Love you too Cherry get some sleep. I'm going to hold my son for a little while." The last time Blair saw before she drifted to sleep was Dean rocking their son and singing AC/DC to him.

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A/N: That got a little _Lord of the Rings_ with the endings. Maybe I'll write a sequel. What do you guys think? Dean, Sam, and Blair called back to the hunt. Hmm...


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